Acetic Acid → Pga1

HRID 1283485Notes

Reaction equation

HRID 1283485 reaction equation
[H][H].[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([OH:27])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:14](=[O:15])[CH2:13][C@H:12]1O.C(O)(=O)C>O>[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([OH:27])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:14](=[O:15])[CH:13]=[CH:12]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5280723AlprostadilHCID 178418361HCID 178418361, compound

Product 1

HCID 5281912Pga1

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Refer to Chart E, wherein E is --CH=CH--, R2 is methyl, R4 is hydrogen, V is --(CH2)5 --, and W is 1-pentyl. A mixture of PGE1, 15-methyl ether, (0.4 g.), glacial acetic acid (9 ml.), and water (1 ml.) is heated under nitrogen at 60° C. for 18 hrs. The mixture is concentrated under reduced pressure, and the residue is subjected to silica gel chromatography, eluting with 25-100% ethyl acetate-Skellysolve B. The fractions shown by TLC to contain the desired product free of starting material and impurities are combined and concentrated to give the Formula-X PGA1 -type title compound.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. washeluting with 25-100% ethyl acetate-Skellysolve B
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b1eb12aba72e4910872ff8645dac78e3
Source dataset
uspto-grants-1976_08
Patent number
US03975404

Reaction notes

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